The Most Unflattering Outfits Karoline Leavitt Has Worn

Before-and-after pics of Karoline Leavitt show how her style has changed since joining MAGA, and it's not for the better. The White House press secretary may be in her 20s, but it's clear she's not interested in following trends, and often shows up in unflattering, outdated outfits. There's a certain skillset many people have for dressing for the occasion, and Leavitt is not one of them. For example, Leavitt will never live down her borderline inappropriate outfit at a UK state dinner during which she wore a one-shouldered gown — something considered a little too risqué amongst royals.

Leavitt also tends to wear clothes that age her, such as boucle jackets and florals that scream coastal grandmother. Perhaps being married to someone 32 years older has rubbed off on the New Hampshire native, as she's often seen in 'fits someone twice her age would gravitate towards. Scouring some online 'zines would definitely give the expecting mom some style tips, and although Leavitt has worn outfits that showed a lot of leg, they were still not worthy of any best-dressed lists.

It must have been Bring Your Baggiest T-Shirt to Work Day on October 8, 2024, because Karoline Leavitt did just that with her huge black top. Not only was the cap sleeve unflattering, but she tucked the shirt into her pants, which created a billowing effect. A smaller size would have suited Leavitt's petite frame much better, and perhaps a longer sleeve would have given the outfit some more structure. Cap sleeves are hard to pull off, especially on a tee that has no definition.

We know that red is the color for Republicans, and Karoline Leavitt made her stance loud and clear on March 16, 2026 outside the White House. And by loud, we mean her red jacket and red flower-printed shirt that were so bright that they were practically neon. The vivid blazer was garish enough on its own, but combined with the busy floral shirt, Leavitt's OOTD was total overkill. A plain button-up would have looked so much more polished without causing onlookers to reach for their sunglasses.

Florals done right can look feminine and breezy, but Karoline Leavitt opted for a 'fit during a March 30, 2026 press briefing that had her resembling a 1950s housewife. The bubblegum pink jacket with large red flowers in a watercolor print reminiscent of a Rorschach test was just so old-fashioned looking, especially with the ballooned sleeves. It also didn't help that the silhouette was baggy and hung off Leavitt's frame like an oversized bathrobe. If this was her idea of welcoming spring, she sure got it wrong.

There are those who travel in style, and then there's Karoline Leavitt, who arrived at Mar-a-Lago in early February 2026 wearing a black tent-like t-shirt dress. Although she was carrying a cute pink Chanel handbag, Leavitt just looked sloppy in the shapeless frock, especially compared to her husband, Nicholas Riccio, who was dressed in a fashionable plaid green suit that was perfect for Florida. We get that Leavitt wanted to be comfy, but at least she could have chosen a color other than bleak black.

Animal prints are worn to get noticed, and Karoline Leavitt certainly succeeded with her zebra-patterned midi dress in March 2023. However, it seemed she was trying for an avant-garde look, and instead of the usual black and white associated with one of our fave striped animals, Leavitt chose a hunter and light sage green color with the lines jarringly close together. The effect was certainly mesmerizing — and dizzying as well. Thankfully, she wore a pair of nude pumps to offset the vertigo-inducing sheath.

Even before she was a White House employee, Karoline Leavitt made some questionable fashion choices that she probably regrets now. In 2018, she took a selfie with a friend at a soccer game, clad in a pair of very ripped jeans. They could have very well been shorts with all the material that was cut out — there were large holes on both legs and slashes above the knee. The distressed look was happening in 2018, but Leavitt took it a bit too far and looked tacky, rather than trendy.